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KMID : 1059520190630040233
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Journal of the Korean Chemical Society
2019 Volume.63 No. 4 p.233 ~ p.236
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Mechanistic Studies of the Solvolyses of Cyclohexanesulfonyl Chloride
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Kang Suk-Jin
Koh Han-Joong
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Abstract
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In this study, the solvolysis of cyclohexanesulfonyl chloride (1) was studied by kinetics in ethanol-water, methanol- water, acetone-water, and 2,2,2-trifluoroethanol (TFE)-water binary solvent systems. The rate constants were applied to the extended Grunwald-Winstein equation, to obtain the values of m = 0.41 and l = 0.81. These values suggested SN2 mechanism in which bond formation is more important than bond breaking in the transition state (TS). Relatively small activation enthalpy values (11.6 to 14.8 kcal·mol-1), the large negative activation entropy values (-29.7 to -38.7 cal·mol-1·K-1) and the solvent kinetic isotope effects (SKIE, 2.29, 2.30), the solvolyses of the cyclohexanesulfonyl chloride (1) proceeds via the SN2 mechanism.
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KEYWORD
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Cyclohexanesulfonyl chloride, Extended Grunwald-Winstein equation, SN2 mechanism, Solvent kinetic isotope effect
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